Phosphorus oxychloride → HCID 73676527, compound

HRID 1679496Notes

Reaction equation

HRID 1679496 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[CH:17][C:18]([CH:20]=[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[CH3:31])=O.[Cl:32]([O-:36])(=[O:35])(=[O:34])=[O:33].C([NH+]1C2=NC3C(N=C2N(CC)C1C#CC=C1N(CC)C2=NC4C(N=C2N1CC)=CC=CC=4)=CC=CC=3)C>N1C=CC=CC=1>[Cl:32]([O-:36])(=[O:35])(=[O:34])=[O:33].[CH3:6][N+:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17]#[C:18][CH:20]=[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[CH3:31]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 54247884HCID 54247884, compoundHCID 86734772HCID 86734772, compound

Product 1

HCID 73676527HCID 73676527, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phosphoryl chloride (1.0 ml) is added to a stirred suspension of 1,3-Bis(1-methyl-2-(1H)-quinolylidene)acetone (0.68 g, 0.002 mol) in pyridine (10 ml). The mixture is stirred for 5 min., then the solid is collected and washed with a little pyridine, then with ether. The dye is converted to its perchlorate salt by solution in methanol, followed by addition of aqueous sodium perchlorate solution. After recrystallization from acetonitrile, the yield of purified dye is 0.30 g (36%) with the melting point indistinct. The following two dyes were prepared by procedures similar to that described above: 1,3-Diethyl-2-[(1,3-diethyl-1H-imidazo[4,5-b]quinoxalin-2-(3H)-ylidene)-1-propynyl]-1H-imidazo[4,5-b]quinoxalinium perchlorate. ##STR20## Recrystallized from acetonitrile. Purified yield 35% mp >300°. 1,3,3-Trimethyl-2-[(1,3,3-trimethyl-2-indolinylidene)-1-propynyl]-3H-indolium perchlorate. ##STR21## Recrystallized from methanol. Purified yield 43% mp. 194°-7° dec.

Workup

  1. customthe solid is collected
  2. washwashed with a little pyridine
  3. additionfollowed by addition of aqueous sodium perchlorate solution
  4. customAfter recrystallization from acetonitrile
  5. customThe following two dyes were prepared by procedures similar to
  6. custom##STR20## Recrystallized from acetonitrile
  7. customPurified yield 35% mp >300°
  8. custom##STR21## Recrystallized from methanol
  9. customPurified yield 43% mp. 194°-7° dec.

Sources & evidence

ORD record
ord-35ded1b2cd4f4b7aa836447de1f176bb
Source dataset
uspto-grants-1978_03
Patent number
US04080496

Reaction notes

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